


Con After Con

by superpotterlock93



Category: Supernatural
Genre: Age Difference, Alternate Universe - High School, Delinquent!Cas, Destiel - Freeform, Jock Dean, John and Mary Live, M/M, Nerd Castiel, Nervous Dean, Not Beta Read, Sabriel - Freeform
Language: English
Status: In-Progress
Published: 2015-06-05
Updated: 2015-07-21
Packaged: 2018-04-03 00:28:36
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 3
Words: 8,456
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/4079662
Author URL: https://archiveofourown.org/users/superpotterlock93/pseuds/superpotterlock93
Summary: <blockquote class="userstuff">
              <p>Dean is a sophomore on the basketball team and once in a while he actually gets to play. Lack of athletic ability aside, he’s well behaved, gets decent grades, has a loving family, the Winchester good looks and the best friend a guy could ask for in Charlie.<br/>Compared to Dean, Castiel is damn near wildly popular. He might look like he camps out at the library and owns a collection of suspenders, but the students know better. People go out of their way to stay on his good side because Castiel Novak does not help just any and everybody. His home life isn’t the best, but this senior has enough tricks up his sleeve to keep his customers happy and paying. He knows what delinquents need and has the means to help. With Gabriel volunteering in the school office, Castiel always gets the heads up he needs to avoid getting caught. Not that anyone ever suspects the teachers’ pet.<br/>These two have no reason to ever talk until Charlie convinces Dean to become Castiel’s latest customer.</p>
            </blockquote>





	1. Pseudo Date

**Author's Note:**

> What happens when a deal with 17 year old con artist turns into some kind of weird almost-date.

Dean glanced over to where Castiel Novak stood at his locker. If there was ever a high school kid who could land Most Likely to Be a Con Man, it was that guy.

He had oversized glasses, a short frame, wore sweater vests over perfectly pressed, button down shirts and slacks. He didn’t look the part at a glance but boy did that help him seem harmless. Well that and his impeccable Teachers’ Pet status. His customers, usually of the troublemaker persuasion, had a much harder time getting out of trouble than he did.

That, more than anything, was what made Dean so nervous to walk up to the boy in the first place. His stomach was in knots and his chest felt too tight. He couldn’t wipe away the fear that something would go wrong. If he got caught, his father would find out and John Winchester’s wrath was no picnic.

There was still time. He could still back out.

Dipping his hand into his pocket, he could feel the Comic Con tickets burning a hole against his thigh. He could practically hear Charlie telling him to just get it over with already. She had already set up a deal with Castiel earlier this week. It hadn’t sounded that hard, he just—.

“Okay, you’ve been just standing there staring for like ten minutes,” Castiel said from right behind him. Dean flinched, not expecting the voice to come from so close. When he turned he could see why. The other boy had been standing right behind him, no concern for personal space whatsoever.

A pair of too bright too blue eyes glared up at him. “Well?” he pressed, “What’s your deal?” Dean took a step back and cleared his throat. The eyes squinted, suspicious now. “I – um – I wanted to ask you something,” Dean fumbled in around his pockets for the tickets, “I – uh – there’s a…hold on. There’s a Comic Con on…” He trailed off at the hand being held up. Castiel pushed away the tickets.

“That’s not how this works. You come to me and make an appointment first.”

“An appointment?” Dean made a face.

“Yes. It’s when you make an agreement to meet someone at a later date.”

“I know what an appointment is.”

“Then don’t ask stupid questions.”

“But I—.”

“When you make an appointment, _then_ we can meet somewhere less crowded to talk about what you need.”

“Oh,” Dean pushed the tickets back into his pocket, “So do – um – do I sign up somewhere?”

“What?” Castiel’s face broke into a smile before he actually laughed, “Sign up? Wow. No. It’s a verbal agreement, kid. Not a doctor’s appointment.”

“Oh. Right,” Dean could feel the embarrassment warming his ears.

“So you free after school?”

“Yeah. After school is good.”

“See you outside the front doors after the final bell.”

The senior walked away with a last chuckle and a shake of his head, leaving the younger boy to stew in his own nerves. Dean shut his eyes and gave a tiny groan before hoisting himself off the lockers. “It could have been worse,” he convinced himself before trudging to his next class.

Two hours of distracted, blank staring later and Dean found himself making his way to the front of the school. Once again, his heart was beating too fast and his palms were too sweaty. He could barely swallow. His throat was so damn dry.

He was only half surprised to find Castiel already waiting at the doors. “Punctual,” he nodded his approval, “That’s a good start.” Dean didn’t know how to respond so he didn’t. Instead he shoved his hands into the pockets of his letterman jacket and waited for Castiel to make the first move.

“Usually I’d find somewhere secluded in school to do this but I’m hungry.”

“I’m sorry, what?” that wasn’t what Dean expected him to lead with.

“Well you have to pay me anyhow, right?” he shrugged, “Let’s get something to eat with some of that cash.”

Dean glanced at the waiting bus and then at Castiel’s retreating back. The boy tossed a look over his shoulder, “Come on! I’ll give you a ride home. Don’t worry.”

On the list of things Dean had prepared for, getting into a car with this guy was not even a consideration. The tickets shifted against his leg and he gave a dark sigh. “Damn you, Charlie,” he muttered before jogging after the senior.

Hip hop music bled out the sound system the moment the car engine revved. Dean raised a brow at the car in question. “A pimpmobile?” he asked before he could stop himself. Castiel flashed him a bitchface that Sam would be proud to call his own.

Dean clambered into the jubilee gold ’78 Lincoln Continental, thinking his dad would die and roll in his grave before setting foot in this gaudy hooptie.

“Seriously?” Dean griped looking around the car. He half expected stuffed pool balls to be hanging around the rear view mirror or maybe fur on the seats. Castiel pulled out of the lot growling a low, “Shut up. There’s nothing wrong with my car. I like it.”

Shaking his head, Dean opted to stay silent during the ride. It was better to stay in this guy’s good graces.

They wound up at a diner near the shopping district. Dean had never been there before, but the smell of food washing over him had his stomach growling. “I know,” Castiel pat his belly, “Me too.”

They ordered a pair of Monterey Jack double burgers with spicy chipotle, fries, onion rings and milkshakes. Dean hadn’t been that hungry until he’d gotten a good whiff of the place. Now he was ready to get elbow deep in something greasy, salty and fatty with cheese.

“This is not usually how things go,” Castiel warned, “Don’t expect awesome dinner every time you want something.”

“I won’t,” Dean smiled spotting the teasing glint in the older boy’s eyes.

“So what exactly do you want, mini jock?” he tugged at his sweater vest.

“My name’s Dean and I’m only a year younger than you. Maybe two for the most.”

“Riveting.”

“Look, I have this thing I need to go to next week.”

“Comic Con,” he nodded, “I remember the tickets.”

“Yeah, well it’s on Saturday but I have to be at school for practice.”

“Not that I don’t want to take your money, but couldn’t you just fake being sick?”

“I’m a notoriously bad liar. I can keep a secret but I just can’t lie to my parents.”

“Couldn’t you leave to go to practice and just…well not go?”

“Coach would go to the office and hunt down my dad’s number to find out. I really don’t want to go to practice.”

 

“And you want me to get you out of it so you can geek out over comics and action figures.”

“Basically yeah. Can you do it?”

“The question is never _can_ I do it. It’s more of a _will_ I do it sort of thing.”

“Will you?”

“A jock on the outside and a nerd at heart,” Castiel leaned back and gave him a good once over, “Don’t come across your breed too often.”

“Is that a yes?”

“’Course. You’re already buying me dinner with my fee, aren’t you? I assume whoever referred you to me told you the cost?”

“Yeah, yeah,” Dean dug out his wallet pushed the bills across the table.

Castiel beamed at the cash and counted it twice for good measure. When he looked up, all gummy grin and dancing eyes, Dean felt something in his stomach flip.

 _Whoa._ Castiel was freaking beautiful when he was happy. He wore it with an openness that made him immediately less intimidating and more so at the same time.

Once Castiel pocketed the money, he pulled a little book out of his back pocket. Dean only needed to lean forward a fraction to see what was inside, but that didn’t make a lick of difference.

Inside the book was a meticulously drawn and organized table filled with absolute gibberish. Castiel went on to fill in the blank spots with strange symbols and letters. Even though he was clearly imputing Dean’s info, Dean couldn’t discern a word. None of it seemed to belong to him.

“No peeping, beautiful,” Castiel murmured as he continued to write.

“I-I wasn’t,” Dean shook his head willing the heat out of his face at the endearment.

“You were. Not that you can understand Enochian anyways.”

“Can anyone other than you understand that?”

“In this small town? Doubtful, but always possible.”

“Okay,” Castiel sat back and read from the book, “You will be absent on Saturday, right?” Dean nodded. “I can find you at Comic Con if I need to contact you?” Dean gave another nod. “And your coach is going to need to believe you have a legit reason not to be there?” Castiel raised a brow when no nod came. “Correct?” he asked. Dean nodded.

“Excellent. Give me your number.”

“Sorry?” his brows shot up, “My…why?”

“So that I can contact you. You think I’m going all the way to Comic Con if I need to find you? That’s only if you don’t pick up your phone. “

Dean called out his number and watched as Castiel jotted more mumbo-jumbo into his book. “The Enochian is coded. Don’t bother memorizing anything,” he said, “I’d like to graduate without getting caught, thank you very much.” He punctuated the final word snapping his book shut.

Dean knew he should think of Castiel as the delinquent he so obviously was. It was hard to once you saw all the work that went into this. It took serious smarts to keep this up for so long, become that successful and never be caught.

When the food came Dean didn’t have it in him to give Castiel a second thought. He was too hungry to have eyes for anything or anyone but his burger. Glancing up, he saw Castiel with his hands clasped and head bowed as he murmured over his food.

“Were you saying grace?” Dean raised a brow once he was done.

“You should try it sometime, you barbarian,” he looked at Dean’s stuffed cheeks.

“Yeah I’m not the prayin’ type, Cas.”

When the silence got too noticeable, Dean looked up to find himself on the other end of the most intense stare he’d ever received. It kind of made Dean want to shrivel up but also kind of made his heart race a little.

“I – um – I’m not saying that there’s anything wrong with praying. It’s just not for me, y’know?”

“I don’t care how pious you are.”

“Then why are you staring at me like that?”

He shook his head and took a sip of his coffee milkshake, “I just…no one calls me Cas.”

“Seriously? Castiel is such a mouthful. I thought most people would.”

“Yeah, well they don’t.”

“Sorry. I won’t—.”

“—No. No, I kinda like it. Cas,” he tasted nickname with a smile flirting on his lips, “Yeah.”

“What do I have to do for this to work?” Dean asked.

“Tomorrow I’ll have a beta read note written for you. Give it to your coach. It’ll have a phone number included for her to call your guardian.”

“What? My dad cannot know I—.”

“Shh. Calm down, baby boy,” Castiel rolled his eyes but looked amused all the same, “Not your real father. I’ll buy a burner out of your fee.”

“So coach will be talking to you?”

“No. I have people. It’s a hub of sorts. People old enough to play the part but young enough to want to.”

“How did you set that up? You’re only in high school.”

“The less you know, the better for everyone,” he smiled around his burger, “You give a legit looking letter to a teacher and leave a number, they’ll use it. I know your coach will.”

Hearing that there was already a plan set Dean’s mind at ease. When they were done, he was too full to move. He could feel the food coma sneaking up on his senses.

Castiel had to half haul him off the seat and lead him back to the car. “Lightweight,” he teased. Too sleepy to be intimidated by the older boy, Dean flashed a middle finger in response.

They were only four blocks from Dean’s house so he barely had time to nod off before they were parked on the curb. “Out,” Cas pointed, “Before you puke on my shit.”

Dean really did feel a little sick. He shouldn’t have eaten that much. He looked over to find concern lining Castiel’s face. “Are you going to be okay?” he asked, “Maybe I should come and…” Dean was shaking his head harder than recommended all things considered.

“My brother, Sammy, he’s home sick with the chicken pox.”

“Wow. Okay then. I’ll meet you at your locker tomorrow with the note. I’ll take care of everything.”

It was strange trusting someone he barely knew, but Dean walked away from the car without a worry about any of it. If he was honest, he was also a little anxious to see Castiel again tomorrow.


	2. The Delivery

**Summary for the Chapter:**

> Today's the day Dean has to deliver the letter to Coach Harvelle. If only he could find Cas and get the damn thing in the first place.

When Dean entered the living room, he couldn’t help the smile tugging on his lips. His brother, in all of his chicken pox-y glory, was just as he’d left him this morning –  no more than a curled up blanket burrito on the couch. The TV was still on and the popcorn on the table was probably stale by now.

“Heya, Sammy,” he dropped his bag and took a seat on the carpet.

“Mmhumhm,” an eyelid cracked open in possibly the best sleepy, one-eyed bitchface Sam had at his disposal.

“How you feelin’?”

“Like crap. I’m itchy all over and these,” he held up mitten covered hands, “are the devil.”

“It’s supposed to keep you from scratching.”

“I know _that_ ,” he huffed, “Do you realize that I’m already behind on all my classes? The term just started.”

“I can go around to your teachers and collect it for you if you want.”

“Would you?” his eyes brightened a fraction, “That’d be awesome Dean.”

“Nerd,” Dean pushed the mop of hair off his brother’s forehead, “Of all the lame things to cheer you up.”

“You have no idea how bored I was today. How long is this thing supposed to last?”

Dean gave a shrug, watching Sam slump further into the couch. The kid looked so miserable and dejected. It had barely been four days since he’d been infected. Dean wasn’t sure how long his brother would last before his frustration spiked and the fretting came.

“Is anyone else home?” Dean peered out of the living room’s archway.

“Dad’s still at work and mom’s at the store picking up some more stuff.”

“Awesome,” he grinned, “Guess what Charlie scored me today?”

“The Comic Con tickets?” Sam sounded bored but there was a fondness in his eyes for the closeted dork in front of him.

“Yeah!” Dean was outright beaming now, “Two more days and I’m gonna be at my first convention.”

“It’s about time. You’ve been talking about that for months. Maybe now you’ll finally shut up about it,” Sam smirked under his blankets.

“Bitch.”

“Jerk.”

“Hey, you wanna see the tickets?” he asked and reached into his pocket anyway.

Sam grabbed his hand before he got the chance. And before Dean could protest, he caught the sound of keys jingling outside the front door. Mary walked in moments after and Dean felt the tension in his gut at almost getting caught.

“Mom!” Sam sounded about as pitiful as it was possible to sound.

“I’m here, I’m here. I got the sweet onion teriyaki chicken salad you wanted, all the orange juice you can drink and fruit.”

“You’re a saint.”

“And I got you a slice of pie from the bakery,” she turned to Dean.

“Seriously. You are a saint, Mary Winchester,” he pulled her over for a big smacking kiss on the cheek.

Though she looked thoroughly unimpressed with the pair of boys attacking the grocery bags, her eye roll was nothing but affectionate.

Dean had been too full to move after dinner with Castiel, but he was never too full for pie.

John had banned him from sweets and fast food since he talked him into joining the basketball team. Today at the diner had been a rare moment and Dean was still riding high on the junk food train. He had every intention of eating that pie before John spotted it and threw it out.

One quick shower and a pie slice later found Dean passed out on his bed in a food coma that was a long time coming.

***

The next morning at school, bright and early, Dean spotted Castiel in the hallway. He couldn’t help the surge of energy that coursed through him in that moment. Comic Con was tomorrow and he was one sick note away from getting the all clear.

As Dean was about to go up to him and ask for the letter, he thought better of it. The boy was busy talking to some chick, his face dead serious. Dean got the feeling that this was business and had the good sense not to interrupt.

When the bell rang before he could get to talk to the senior, he had to talk himself down. There’s no need to worry. It was fine. There was no rush. He’d just get it some other time today. It was still early.

But when recess came and went without a trace of Castiel, Dean sat through third period feeling more bothered by the minute. The day was nearly half done and he had no idea where he’d find the other boy. He needed that letter before the end of the day or it would be totally useless.

When lunch time rolled around, he knew he had to work fast. Castiel never ate in the cafeteria and Dean had no idea which classes he took. If he didn’t find him at lunch, he’d have to catch him after school. That would be even more difficult.

Dean spent nearly a good half an hour scouring the halls looking for messy haired brunettes, sweater vests and khakis. _He has to be around here somewhere. It’s not like he can leave the compound._ It only then occurred to him that maybe Castiel did. How is it that he’s expecting the school’s resident con artist to follow the damn rules?

Dean groaned. The thought of _What if I don’t find him at all today?_ turned his search considerably more frantic.His panic grew and gnawed at him the longer he looked. In the end, the last place he hadn’t looked was the cafeteria. The only reason he went in was as a last, desperate resort.

It was while scanning the room that a low whistle caught his attention. Somehow Dean could tell it was meant for him without turning. The moment his head whipped around at the sound, he spotted him.

There was that asshole Castiel motioning for him to come over to the other side of the cafeteria. Dean didn’t know if he was more frustrated or relieved but he hurried over all the same. They met at the door leading to the yard. Dean had a few choice words for the boy about how damn hard it was for customers to find him and how—.

“What took you so long?” Castiel demanded, “I waited almost an entire lunch period looking for you.”

“Me?” Dean snapped, “ _I_ was looking for _you_.”

“I figured you’d eat lunch in the cafeteria like everyone else.”

“And I figured you’d be avoiding the cafeteria like you always do.”

Castiel stopped in his tracks. “…Why in heaven’s name would you even notice that?” he frowned but waved away the question before Dean could answer, “Never mind. I skipped my lunch date with my brother to meet you.” He opened his mouth, looking like he wanted to say something else, but stopped himself before it could get out.

Shaking his head, Castiel led the way over to a couple of the benches out on the lawn. It was kind of the perfect lunch spot hiding under the cover of trees. Dean half wondered if this was where he usually ate lunch when he wasn’t in the cafeteria.

Castiel took a seat and started organizing his things around him. Dean stayed standing. The silence got more and more uncomfortable the longer he waited. It seemed like Castiel didn’t intend on actually doing or saying anything concerning the anxious boy standing beside him.

“So you – er – you got anything for me there, Cas?” he shuffled from foot to foot.

“Yeah,” he spared a tiny smile over the nickname, “One beta read excuse letter complete with your dad’s signature, a fake contact number all folded inside his stationary.”

“Wait, what?” Dean took the offered envelope, “His signature? And stationary?”

“I found out where your dad worked and got my hands on some envelopes with the company name on it,” Castiel shrugged.

“In one night? How did you—?”

“—The less you know, the better. I got his signature off your file in the office. It all looks pretty legit.”

Dean turned the envelope around in his hands, “You’re good.”

“That’s why I’m still in business. You’re welcomed, by the way.”

“Oh. Right. Um…thank you,” Dean quickly scanned the letter and smiled to himself, “I can’t believe—. God, I could kiss you.”

“Now now,” Castiel leaned back in his seat, “That costs extra, kiddo.”

Dean’s head snapped up at that. He genuinely couldn’t tell if Castiel was joking or not, but it didn’t matter to his face since it flushed at the possibility anyway.

Castiel took a look at his watch and then back up at Dean. “Have you eaten yet?” he asked even as he pulled a brown paper bag from his satchel. Dean shook his head, now realizing that he’d wasted nearly all of this time looking for Castiel. His stomach growled on the heel of that thought.

“The bell’s going to ring soon. Heading into the lunch line now is a waste,” Castiel said and motioned for Dean to sit with him at the picnic table. He busied himself with putting a sandwich near Dean, opening a packet of potato chips in the middle for them to share and getting a pudding cup out.

“The pudding is mine,” Castiel warned, “Don’t even pretend to dream about imagining thinking about looking at it.”

Dean forced down the urge to grin. Big, bad Castiel Novak – CEO  of his own pay-per-con business – was possessive over his PB&J flavored pudding cups. It was equal parts surprising and adorable.

“First you take me out for dinner and now a picnic lunch?” Dean bit into his sandwich, “If you wanted a date, you could have just asked.”

The stare Castiel fixed him with was so absolute, so unwavering, so intense that Dean started to wish he hadn’t made the joke at all. He’d never noticed how impossibly blue those eyes were until he was under Castiel’s relentless focus. Then came his suspicious squint.

“Was that…a flirtation?”

“I-I no. No I was just joking.”

“Oh,” his stare softened to something more accepting, “Alright.”

Castiel bowed his head and clasped his hands to say a quiet grace under his breath. This time, Dean waited until he was done before taking another bite. And if Castiel’s lips twitched in a tiny smile of approval, that most definitely didn’t make something in Dean’s stomach do a back flip.

It was a simple turkey sandwich with mayo, cheese, lettuce and tomato but Dean’s very vocal stomach thought it was heaven. He knew he shouldn’t with his new diet, but he grabbed a handful of potato chips anyways.

Castiel wasn’t much of a talker. He seemed to like watching the younger kids playing off in the distance better. There was a sense of serenity to his expression when he looked out at them. Dean didn’t want to disrupt his silence so he kept his thoughts to himself. He was content to just sit and pretend _not_ to watch Castiel from the corner of his eye.

Although they’d barely spoken a word to each other, there was an air of acceptance between them. Dean didn’t feel quite like a stranger that Castiel only tolerated because he wanted his business. Not as much as he did yesterday at least.

Dean actually felt a pang in his chest when the bell rang. He wasn’t ready to leave just yet for some reason. He knew it was unlikely that he and Castiel would ever have reason to talk again and that, more than anything, dimmed his mood.

He got to his feet, “So – uh – thanks for lunch, Cas. You really didn’t have to.”

“It was the decent thing to do, as my father says,” he gave a shrug, “but you’re welcomed.”

“Maybe I’ll see you around?” Dean adjusted the bag onto his shoulder better.

“Maybe,” Castiel was too busy packing up his trash to look up, “This is a big school.”

“Oh,” Dean recognized the rejection and felt his mood drop all the way to his toes. Somehow he still managed a low, “Yeah. You’re totally right.”

Castiel hoisted his satchel over his head and gave a polite nod before disappearing back into the building. Dean stood rooted on the spot for a while before he took a breath and did the same.

There was no reason to bother with Castiel anymore. He had his money and Dean had his excuse. The deal was done and Dean had a letter to deliver.

It wasn’t hard to find Coach Harvelle. Dean always knew exactly where she was at every hour of the school day. She was predictable and loved routine. It reminded him so much of his father that he was convinced that she might have served in the military too.

If anyone knew that he had the coach’s schedule memorized, they might call it creepy. It wasn’t, honest. It was more of a necessary burden if anything else. Dean had to always know where she’d be if he wanted to successfully avoid her.  The coach had a habit into forcing him into extra training.

Sam loved staying active and doing new exercises. Sports was their dad’s thing. Dean had no interest in anything that involved running or working out. He didn’t think he should be using up unnecessary energy unless something or someone was chasing him.

Dean kind of missed the good old days.

Back when his dad was an active Marine, they had moved around a lot and it had been the perfect excuse to duck out of extracurricular activities. Dean had been fully content to avoid schoolwork, skip classes and flirt with whichever girls caught his eye in the town-of-the-month.

There was a certain comfort to knowing he wasn’t going to stick around long enough to deal with petty things like consequences. He could get away with all the delinquency in the world and not worry at all.

Now that his father was no longer active, they’d bought a house and things became a bit more permanent. They’d settled down. With a permanent school, Dean was forced to realize how behind he was in his classes. He’d been playing catch up ever since.

These days he was a model student in a way his past teachers would never believe. He had no choice if he wanted to graduate. The one thing he slacked off on was basketball training.

He cringed at the idea of – for the first time in years – _purposely_ looking for Coach Harvelle. Like on _purpose_.

He knew for a fact that since it was just after lunch, she was likely in the office finishing up her talk with Principal Singer.

When he entered the waiting area, a glance at his watch let him know to wait for seven minutes. The kid behind the office counter looked at him with open curiosity. He didn’t say a word to Dean but he continued chewing on his red liquorice nonetheless. Once the seven minutes were up, Dean straightened up and Coach Harvelle came out.

“Hey there, Winchester,” she gave him a gruff pat on the back that may have actually knocked out a chunk of his lung, “What can I do you for?”

“I…” he wheezed, “Can’t make it to practice tomorrow.”

“Do you have a—?” she stopped at the envelope thrust into her hands.

The kid behind the counter gave a sly smile to himself, seemingly more interested than before. Dean made the effort to ignore him. He only had eyes for the coach as she scanned the note.

“God, I hate the dentist,” she made a face and stuffed the letter back into the envelope, “Any procedures with drills are the worst. I don’t envy you, Winchester.”

“I – uh – I don’t envy me either?”

“Guess I won’t be seeing you tomorrow then,” she gave a sigh, “And I was really hoping to work on your aim some more.”

“There’s always next week,” Dean’s eyes darted to the note and back to the stern face staring him down to the bone.

“Next week it is,” she gave a curt nod and strode off.

Dean didn’t realize how nervous he’d been feeling until she left the office. It was almost anticlimactic really. He’d been wound up about this whole situation and it had been easy.

That wasn’t to say that he was balls-y enough to pull anything like this again. There was something about Coach Ellen Harvelle that scared him a little. Lying to her was almost as hard as lying to his dad.

“Good job,” the kid at the counter grinned, “You almost didn’t piss yourself.”

“Shut up. This has nothing to do with you.”

“It might have if you had messed up that lie,” he shrugged, “My brother wouldn’t have been too happy with you.”

“You’re Cas’s brother?”

“Cas?” he chuckled, “He lets you call him that? Gives me shit for calling him Cassie.”

“He lets _you_ call _him_ that?”

“Nah. He’s been bitching about that for years,” the boy stuck out his hand, “I’m Gabriel. Cassie’s better looking bro.”

“Oh yeah?” he scoffed, “Dean.”

“I know. I’m the beta reader. I worked hard on that bad boy last night,” he gave a wink.

 _So that’s why he was so interested._ Dean looked at the playful boy and couldn’t help but notice how different he was to Castiel. Gabriel was certainly more open and ready to flash a grin.

The boy grabbed his backpack and made it around the counter to meet Dean. “Let’s get to class,” Gabriel jabbed a thumb at the door, “We’ll talk on the way.” He barely gave Dean time to react before bounding away, a ball of sugar rush energy.

“So. Winchester, huh,” Gabriel tossed a glance across, “Any relation to Sam Winchester by chance?”

“You know Sammy?”

Gabriel smiled, “Yeah. When the middle school is running slow, he helps out in this office sometimes.”

“You two friends?”

“Not really. Kind of. We talk,” he shrugged, “but I haven’t seen him around lately.”

“He’s sick at home. Chicken pox.”

Dean nearly missed Gabriel’s abrupt halt. He threw a glance over his shoulder to find the boy simply standing in place, frowning to himself. With concern lining his face, his entire persona had sobered up. In the moment, Gabriel looked more like his brother than ever before.

“He hadn’t said a thing.”

“Well if you know my brother, you know he’s usually the suffer-in-silence type.”

“I hated having chicken pox,” Gabriel frowned, “I bet he’s bored.”

“Yeah. He’s been doing nothing but watching day time TV all day and complaining about reruns.”

“Is it cool if I come see him?” Gabriel asked, “I could get his homework for him and cheer him up a bit.”

“That’d be great. He might like the company.”

“Plus he’s probably tired of seeing your pretty mug all day when he’s all pox-y,” his teasing tone slipped back as easily as it had left.

“He probably is,” Dean ran his fingers through his hair and shot Gabriel a winning smile.

“You’re alright, Dean-o,” he laughed big and loud, “You’re alright.”

Dean liked how easy it was to joke around and kid with Gabriel, but he knew it was nothing like hanging with Castiel. _Oh well. Who’s to say I can’t be friends with this brother? He’s nice enough and he’s friends with Sam._

When the bell rang after school, Dean went to the front doors to meet Gabriel as they’d planned. He wasn’t surprised that Gabriel wasn’t there yet, but he was surprised to find a pair of too blue eyes peering at him over glasses.

“Cas. Hey.”

“Hello, Dean,” he gave a nod and turned his attention back to the door.

“You waitin’ on Gabriel too?”

“Yes,” the answer came slow with suspicion, “How did you know?”

“I’m waiting too. I’m supposed to head to my house with him right now.”

“You and my brother? Why would you want to hang out with him?”

“What’s wrong with that? He’s funny. I like him. Besides he’s coming to keep my sick little brother company so he can’t be so bad.”

“He’s not,” Castiel shook his head, “I didn’t mean for it to sound that way. I just…it’s weird.”

“That I would want to hang around Gabriel?”

At that moment, the boy in question came out the front door with stacks of booklets. “I got the homework. Let’s roll,” he beamed. Dean tried to take some of the booklets from him but Gabriel shook his head, “It’s all good, Dean-o. I can handle it.” Dean wasn’t so sure considering that Gabriel’s hands were shaking a little under the weight.

Castiel rolled his eyes at that, but a small smile was creeping onto his features in spite of it. They followed him to his car and he started driving to Dean’s house. Somewhere during the ride, Gabriel began looking between the two older boys. He was only a freshman but he was no fool.

“Cassie—.”

“Don’t call me that.”

“—I can’t help but notice that you know _exactly_ where to go,” he said, “Y’know I figured that our Dean here would have to give you directions.”

“Gabriel,” the tone was a warning.

“I mean it’s not like you’ve been here before, right?”

Dean was smart enough to know to keep his mouth shut when Castiel’s eyes met his in the rearview mirror. It was no more than a quick glance, but he got the message loud and clear.

“We happened to be talking before you showed up, if you remember,” Castiel said. And Dean noticed that it wasn’t a lie. They had been talking. While he didn’t explicitly say that Dean had given him directions, it was enough that Gabriel would assume it.

When Castiel parked at the curb, Gabriel looked around. “This is where you live? Seriously?” he turned around to look at Dean, “We’re practically neighbors.” Dean’s eyes slid over to Castiel but the other boy wouldn’t meet his gaze.

That was fine. He had Gabriel here. Dean could get all he needed out of him and Castiel wouldn’t be there to shut him up.

Once they climbed out of the car, Dean asked loud and clear, “So neighbors, huh? How far from here exactly do you live?” He could feel Castiel’s eyes on him the whole time. Gabriel glanced back at his brother and when he responded his voice was just as clear. “It’s only two blocks away,” he said, “Maybe when we’re done here you can walk me home and I’ll show you.”

“That’s no problem. Let’s head in and see Sammy.”

Castiel drove away without another word to either of them. Gabriel seemed more than amused by that and followed Dean up the walkway with a pep in his step.

“Dean, is that you?” Sam called when the door shut behind them.

“Yeah! And I brought something for you.”

When Dean entered the archway, he could see Sam sitting up from the couch, looking eager as ever. The moment his eyes slid to the side, that eagerness faded and the color drained from his face.

“Gabriel Novak?” his voice was quiet and his hands quickly pushed his sleeves down to cover his pox-y arms.

“Hey Sammich,” Gabriel came over and dumped the booklets onto the coffee table.

“You’re here. In my living room. Why?”

He grinned and teased, “Trust me. If I’d known how much work you’d missed I wouldn’t have offered to get it.”

“You got my homework for me?” a small smile picked up the edges of his mouth, “Really?”

“Sure thing,” Gabriel plopped onto the couch not shy about getting into his space, “What are friends for?”

“Didn’t realize we were friends,” Sam admitted, “But thank you.”

Gabriel reached out to pat the side of Sam’s hair that was sticking out. “You’ve been sleeping all day, haven’t you?” he asked. Dean was sure this was the first time he’d ever seem Sam blush like that before. Gabriel _tsked_ and fussed over him, “Your hair is about as big a mess as mine was when I had the pox. Oh and thanks for letting me know you were sick by the way.”

“I didn’t think it would make a difference.”

“Yeah, you wouldn’t,” Gabriel scoffed.

Dean wouldn’t have minded hanging out with them, but he got the feeling that he shouldn’t stay. Although he wasn’t sure about Gabriel felt, Dean could tell that Sam was harboring a crush of his own.

The kid was only eleven and, advanced classes or not, Dean didn’t feel comfortable with the idea of him dating a high schooler. He knew it wasn’t his call and he knew that Gabriel probably didn’t return Sam’s feelings, but the possibility made him uneasy.

He didn’t want Sam to get hurt, but he could see that his brother was already far gone.

From the kitchen Dean could see into the living room. It wasn’t hard to spot the way Sam looked up to Gabriel. Sam had always pretended that getting attention from Dean and his friends didn’t matter to him but it did. He liked the attention of the older boys.

While Dean knew that Sam looked up to him, he’d never seen him like this. He was all goofy, dimpled smiles and wide, hazel eyes. He could spot the pink staining the boy’s cheeks from the other room.

Gabriel looked totally unaffected, like he was used to this. Or like he didn’t notice. He was talking to Sam about something and his hands were all over the place, animated as ever. Sam simply leaned back against the armrest and watched, a grin plastered across his face.

It was the least miserable Dean had seen him since he’d gotten sick. For now, he was fine with that.

**Notes for the Chapter:**

> Feel free to share and comment :D


	3. Meeting the Family

**Summary for the Chapter:**

> Not only does Sam have to suffer through Gabriel meeting his parents, but Dean gets to meet yet another of Castiel's brothers. This one is as different from Cas as Gabriel is but Dean isn't sure how he feels about that fact yet.

It had gotten late and Sam figured it was only right to invite Gabriel to stay for dinner.

Honestly it wasn’t that big a deal to either Winchester, but Gabriel seemed to think it was. He insisted on helping Dean set the table even though he was pretty clumsy about the whole thing.

“You’d think you haven’t done this before,” Dean teased.

“I haven’t,” Gabriel shot him a wry smile, “I have one sister, two brothers and one dad barely holding us together.”

“Not too many family meals?”

Gabriel scoffed, “More like none. There’s too much fighting between my siblings. I try to stay out of it.”

“So you just abandon ship and avoid dinner?”

“Paper plate meals in my room do just fine, Dean-o. I’m not too fancy. Plus I always got enough candy stashed away for desert.”

Once Mary and John returned home they didn’t think to object to Gabriel joining them for dinner. Hell they were happy to find that one of Sam’s friends was there to visit. They were even happier to see that Sam was, for once, not griping about how bored or lonely or itchy he felt.

The lack of bitching was a welcome reprieve for everyone, Sam included.

During the meal, Gabriel kept up his talkative spirit.

Dean was starting to see exactly how the differences between the Novak brothers worked. Castiel was the brains and face of the business, but he wasn’t especially good with people. Gabriel was perfect for the communications aspect; writing correspondence, faking letters, all of that good stuff.

In fact Gabriel was so much of a charmer that even John took a shine to him. That was saying a lot since John didn’t particularly like the friends Dean tended to bring home.

Something about Benny seemed to rub him the wrong way and he complained about it every chance he got. John didn’t mind Charlie so much but he frowned upon her life choices. By life choices he meant Charlie insisting on dating ‘that asshole kid, Bela’.

Bela was no longer allowed in the house after pocketing one of John’s military grade knives. No one knew how, but she’d managed to sneak it back after being confronted. Up to this day she maintained that she didn’t do it since no one could prove otherwise. That didn’t matter. Everybody knew it was her.

With Gabriel’s suspicious operations with Castiel, Dean thought his dad would sense there was something sketchy about him in a heartbeat. In the end it was a waste of worrying. It seemed like tricking people was Gabriel’s thing. He was surviving the dinner just fine with minimal suspicious looks from John.

Their parents did as parents usually did and put him through a round of 20 Questions. This was where Sam took the initiative to huff, puff and groan at each question. He sunk further into his seat with each question, bitchface growing more severe by the minute.

They grilled Gabriel about school, family and life goals. Halfway through dinner, Sam was begging them to – _please_ for the love of God – stop harassing his friend. Gabriel waved off the exasperated boy, apparently enjoying the attention.

After dinner the boys all settled in to finish the rest of their movie and share a pint of chunky monkey. Gabriel, once again, had chosen a spot on the couch between the Winchesters. It was the perfect spot to reasonably argue that he should be the one to hold the ice-cream tub.

In retrospect that was a terrible decision. Gabriel had the ability to somehow steal every single damn piece of chocolate that showed up before anyone noticed. Overall, everyone else wound up with more monkey than chunky.

As the movie started to die down, Sam began squirming in his seat. He fidgeted and fidgeted, growing ever restless. Soon enough he began rubbing at his arms as discretely as he could.

“I see you, Sam Winchester,” Mary frowned from the kitchen, “Dinner’s over, mittens on.”

“But mom—.”

“Mittens on.”

“So embarrassing,” he grumbled but shoved them on all the same. His face burned red when Gabriel glanced over.

“Getting chicken pox is kind of unfair, y’know,” Gabriel turned to Dean, “It makes you look so gross.”

Over Gabriel’s shoulder, Dean caught the hurt that flared up in his brother’s eyes. Before he could say anything, Gabriel continued. “But then of course there’s this asshole,” he jabbed a thumb over at Sam, “still looking cute as a fuckin’ button over there.”

Dean couldn’t make out the words from where he sat, but he was sure Sam had muttered, “Shuddup, Novak.” There was not a shred of heat to the words. In fact it was hard for anyone to take it to heart with Sam’s smug freakin smile taking up half of his face.

“He’s also terrible at taking a compliment,” Gabriel huffed polishing off the last of the ice cream. He got to his feet and gave a big stretch, “Well it’s been fun hanging out with you two chuckleheads but I gotta head out.”

“What? Already? But it’s only…” Sam glanced at the clock, “Oh.”

“Yeah. _Oh_ ,” he smiled, “But maybe if my brother doesn’t need my help with anything, I might drop by tomorrow.”

“Okay,” Sam perked up a fraction, “That’d be cool.”

“Yeah man,” Dean got up and collected everyone’s spoons, “It was awesome having someone other than this nerd to hang with.”

“Shut up, jerk,” Sam hauled a pillow at his head hard enough that he stumbled a little.

“Boys!” John glared from the kitchen, “For God’s sake. We have company.”

 “Sorry, sir,” Sam called back but the middle finger he flashed Dean was well hidden behind the couch. Dean smirked all the same, mouthing ‘Bitch’ when their parents weren’t looking.

He sauntered into the kitchen, tossed out the carton and handed Mary the spoons. All the while Gabriel thanked her for letting him stay for dinner.  Then he complimented John’s baked chicken and whiskey sauce once again.

Dean half wondered how genuine that charm was since Gabriel shot it at everyone within a two mile radius.

“Later, Winchesters,” the boy called over his shoulder with a wave and a grin. Sam was the only one to wave back. “I’ll text you tomorrow to let you know if I’m coming or not, alright Sam?” Gabriel didn’t see his nod since he was already half way out the door.

With only two blocks between their houses, neither boy was in any great hurry. They settled into a stroll, too full from desert to notice the initial silence.

“So – uh – are you and your brother close?” Dean asked.

“I’ve got two of ‘em, but I’m pretty sure you mean Cassie amirite?” Gabriel waggled his brows.

“Yeah. I – what’s with the eyebrows?”

“Oh you know,” he looked too smug for his own good, “You and Cassie.”

“Me and him what?”

“You got a thing for him.”

“A thing? For Cas?” Dean frowned, “I’m straight, Gabriel.”

“You’re kidding,” he sniggered, “ _You_?”

“Yes me,” he glared, “It’s not _that_ impossible to believe, you ass.”

“Oh. You’re serious?”

“Who jokes about that?”

“I dunno but what with the way you are around Cassie…” he trailed off with a tiny shrug, “I figured you might.”

Dean felt his face heat up in spite of himself. Was Gabriel the only one who figured that? Did Castiel think the same? God, he hoped not. He was enough of a blundering mess around the older, intimidating senior without making him uncomfortable with something like this.

Castiel may have been flirty from time to time, but Dean knew he hadn’t meant it. It was more of a throwaway line or two for teasing sake. It was messing-with-the-sophomore type of stuff. Dean had done the same. It meant nothing.

“So you honestly don’t see him like that?” Gabriel raised a brow.

“I’m not blind. He’s attractive, sure. Anyone could see that,” Dean scrubbed the pads of his fingers across his neck, “But I’m not attracted to him.”

“Shame.”

“Why? He feels the same, doesn’t he?”

“Oh no, buddy. I know you for a grand total of one day. I’m not getting in the middle of this.”

“But—.”

“You wanna know if my brother thinks you’re cute or somethin’? Ask him yourself.”

Gabriel’s walk hastened considerably at this point. Dean didn’t comment on it but followed him anyway. When they turned to a small, modest house, he really didn’t need Gabriel’s grand announcement. He could tell that it was his.

Castiel sat outside on the porch steps with a guy with hair just as dark if not more tamed. Gabriel led him over to them and flapped a hand, “This is my other loser brother. He’s home from college this week.”

“Hey,” he got up and stuck out a hand to shake, “Michael Novak. Far cooler than these two idiots put together.”

“Dean Winchester.”

“You’ve got some height on you, kid,” the pale eyes gave him a once over, “You already a senior, Dean?”

“He’s only a sophomore,” Castiel cut in. His jaw was tense under the strain of the words. Dean had the presence of mind to see that Castiel wasn’t in the best of moods. He couldn’t tell if he simply didn’t get along with Michael or if it had something to do with him.

“I should – um – get back,” he forced a smile.

“Oh already?” Michael plopped back onto the porch step, “Don’t let Grumpy Cassie scare you off.”

Castiel shot him a filthy glance, embarrassment coloring his cheeks. Gabriel looked from Michael’s dancing eyes to the scowl on Castiel’s face. He’d witnessed enough fights between his siblings to sense when one was on the verge of starting up.

“Uhh…actually I think Dean oughta head home. His parents’ll start wondering what’s taking him so long,” Gabriel gave him a pat on the back and a meaningful look.

“That’s a damn shame,” Michael said but his eyes were on Castiel.

“Yeah, shame,” Castiel muttered.

“Well don’t be a stranger. Barely get to meet a lot of my brothers’ friends,” Michael grabbed Castiel in a headlock, “I’m starting to think this one doesn’t have any.”

“That’s between you and Cas,” Dean smiled at the scuffling pair, “Nice meeting you anyhow.”

“The pleasure is mine,” Michael released his brother to shake his hand and flash a sunny smile.

Without thinking, Dean tensed. He knew that smile. He knew it too well. It was all allure, flirtation and self assurance. Once upon a time Dean had aimed that very same look at girls at his old schools. Being on the other end of it made him uncomfortable to say the least. He released the warm hand in his.

“Quit it, Mike,” Gabriel gave his brother a small kick, “He’s doesn’t play for your team.”

“Seriously? Wow, I am so sorry.”

“It’s okay I guess. Seems like a common mistake lately.”

“Well I just figured…” Michael glanced at Cas and shook his head, “Nevermind. Sorry.”

“Really. It’s fine,” he said, “But I really have to head back now. See you around?”

“Alright. Get home safely, Dean,” Castiel got to his feet.

“Thanks, Cas,” a small smile made it onto his face, “I will.”

“And enjoy basketball practice tomorrow,” Gabriel grinned and wiggled his brows.

“I definitely will,” Dean laughed in the wake of Castiel’s amused scoff.

That reaction was enough for Dean. Dealing with a pissed off Castiel came with the kind of tension that could put people on edge. Now that the older boy seemed to be in a much better mood, Dean felt his body relax a fraction more with every step he took toward his own house.

**Author's Note:**

> Updated every week.  
> Please leave some kudos and feedback :D


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